Flights to Chicago from CA $ 370*
United's most popular flights to Chicago (ORD)
flight_takeoff
flight_land
CA $
Toronto (YYZ)to
Chicago (ORD)2026/06/13 - 2026/06/20
from
CA $ 404
Viewed: 16 hours ago
Roundtrip
Economy
Vancouver (YVR)to
Chicago (ORD)2026/07/03 - 2026/07/07
from
CA $ 608
Viewed: 17 hours ago
Roundtrip
Economy
Calgary (YYC)to
Chicago (ORD)2026/05/21 - 2026/05/25
from
CA $ 370
Viewed: 17 hours ago
Roundtrip
Economy
Montreal (YUL)to
Chicago (ORD)2026/06/09 - 2026/06/23
from
CA $ 422
Viewed: 17 hours ago
Roundtrip
Economy
Winnipeg (YWG)to
Chicago (ORD)2026/06/08 - 2026/06/12
from
CA $ 905
Viewed: 10 hours ago
Roundtrip
Economy
Ottawa (YOW)to
Chicago (ORD)2026/07/09 - 2026/07/13
from
CA $ 910
Viewed: 1 day ago
Roundtrip
Economy
Halifax (YHZ)to
Chicago (ORD)2026/06/09 - 2026/06/13
from
CA $ 905
Viewed: 11 hours ago
Roundtrip
Economy
Edmonton (YEG)to
Chicago (ORD)2026/06/13 - 2026/06/17
from
CA $ 902
Viewed: 17 hours ago
Roundtrip
Economy
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
Business class deals on flights to Chicago (ORD)
flight_takeoff
flight_land
CA $
Toronto (YYZ)to
Chicago (ORD)
2026/05/30 - 2026/06/07
Roundtrip
Business
from
CA $ 992
Viewed: 3 hours ago
Vancouver (YVR)to
Chicago (ORD)
2026/05/21 - 2026/05/25
Roundtrip
Business
from
CA $ 1,637
Viewed: 9 hours ago
Calgary (YYC)to
Chicago (ORD)
2026/05/23 - 2026/05/27
Roundtrip
Business
from
CA $ 1,241
Viewed: 1 day ago
Montreal (YUL)to
Chicago (ORD)
2026/07/08 - 2026/07/13
Roundtrip
Business
from
CA $ 628
Viewed: 11 hours ago
Winnipeg (YWG)to
Chicago (ORD)
2026/06/23 - 2026/06/23
Roundtrip
Business
from
CA $ 1,189
Viewed: 12 hours ago
Ottawa (YOW)to
Chicago (ORD)
2026/07/09 - 2026/07/13
Roundtrip
Business
from
CA $ 1,246
Viewed: 1 day ago
Halifax (YHZ)to
Chicago (ORD)
2026/07/10 - 2026/07/18
Roundtrip
Business
from
CA $ 1,252
Viewed: 1 day ago
Edmonton (YEG)to
Chicago (ORD)
2026/06/17 - 2026/06/24
Roundtrip
Business
from
CA $ 1,448
Viewed: 1 day ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
Things to do after your flight to Chicago (ORD)
In Chicago, you can have it all
Chicago is the perfect urban getaway. “The Second City” is home to stunning architecture, endless shopping on the Magnificent Mile, one of the world’s most dynamic dining scenes, and a collection of critically acclaimed museums, all nestled on a lakefront lined with running trails and natural sand beaches.
Chicago’s top attractions
- Stroll through Millennium Park and take in the art and architecture, including Cloud Gate, which is also known as “The Bean,” Crown Fountain and Lurie Garden.
- Go shopping along the Magnificent Mile on Michigan Avenue.
- Discover the fun attractions at Navy Pier, including a large Ferris wheel, theater and carousel.
- Enjoy a day with the kids at the Shedd Aquarium and Lincoln Park Zoo.
- Tour Wrigley Field, home of the Chicago Cubs and one of the oldest baseball parks in the U.S.
- Take in city views from the Willis Tower’s Skydeck.
- Enjoy Chicago's family atractions.
Chicago is a popular place to visit all year round, though visitors will find that spring and fall have the most pleasant weather. Summertime activities include Lollapalooza music festival, Taste of Chicago, Chicago Jazz Festival and the Chicago Gay Pride Parade. Other major events throughout the year include the Chicago Underground Film Festival in the spring, the Chicago International Film Festival in the fall and the Magnificent Mile Lights Festival in the winter.
Find your vacation package to Chicago with United Packages.